Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine

Autores
Agotegaray, Mariela Alejandra; Dennehy, Mariana; Boeris, Mónica Alejandra; Grela, Maria Alejandra; Burrow, Robert A.; Quinzani, Oscar Valentín
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The copper(II) ternary complexes of the non-steroidal anti-inflammatory drug Fenoprofen (Hfen) and the biologically relevant molecules imidazole (im) and caffeine (caf) as auxiliary ligands were investigated as novel anti-inflammatory agents. The new copper(II) complexes with formula [Cu(fen) 2(im) 2] (1) and Cu 2(fen) 4(caf) 2 (2) were synthesized from the dinuclear complex [Cu 2(fen) 4(dmf) 2] and characterized by IR, UV-Vis, EPR spectral and elemental analysis. The molecular structure of complex 1 was determined by X-ray crystallography. Both complexes 1 and 2 present enhanced and prolongued anti-inflammatory properties against the parent drug calcium Fenoprofenate, Ca(fen) 2·2H 2O, with a better performance for complex 1. Ternary complexes are potential models for several mono and poly-nuclear metal enzymes. The measured superoxide dismutase (SOD) mimetic activities of the complexes indicated a higher SOD mimic activity for complex 2 (IC 50 of 0.24 μM) than complex 1 (IC 50 of 0.70 μM), and also than the native enzyme evaluated by the same method (IC 50 of 0.480 μM). The catecholase activity of the complexes toward the aerobic oxidation of 3,5-di-tert-butylcatechol (dtbc) onto 3,5-di-tert-butylquinone (dtbq) showed that both complexes have moderate catalytic oxidase activity.
Fil: Agotegaray, Mariela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Dennehy, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Boeris, Mónica Alejandra. Universidad Nacional de La Pampa. Facultad de Ciencias Veterinarias; Argentina
Fil: Grela, Maria Alejandra. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata; Argentina
Fil: Burrow, Robert A.. Universidade Federal de Santa Maria; Brasil
Fil: Quinzani, Oscar Valentín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Materia
ANTI-INFLAMMATORY
CATECHOLASE
COPPER
FENOPROFEN
SOD
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/199504
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/199504
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeineAgotegaray, Mariela AlejandraDennehy, MarianaBoeris, Mónica AlejandraGrela, Maria AlejandraBurrow, Robert A.Quinzani, Oscar ValentínANTI-INFLAMMATORYCATECHOLASECOPPERFENOPROFENSODhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The copper(II) ternary complexes of the non-steroidal anti-inflammatory drug Fenoprofen (Hfen) and the biologically relevant molecules imidazole (im) and caffeine (caf) as auxiliary ligands were investigated as novel anti-inflammatory agents. The new copper(II) complexes with formula [Cu(fen) 2(im) 2] (1) and Cu 2(fen) 4(caf) 2 (2) were synthesized from the dinuclear complex [Cu 2(fen) 4(dmf) 2] and characterized by IR, UV-Vis, EPR spectral and elemental analysis. The molecular structure of complex 1 was determined by X-ray crystallography. Both complexes 1 and 2 present enhanced and prolongued anti-inflammatory properties against the parent drug calcium Fenoprofenate, Ca(fen) 2·2H 2O, with a better performance for complex 1. Ternary complexes are potential models for several mono and poly-nuclear metal enzymes. The measured superoxide dismutase (SOD) mimetic activities of the complexes indicated a higher SOD mimic activity for complex 2 (IC 50 of 0.24 μM) than complex 1 (IC 50 of 0.70 μM), and also than the native enzyme evaluated by the same method (IC 50 of 0.480 μM). The catecholase activity of the complexes toward the aerobic oxidation of 3,5-di-tert-butylcatechol (dtbc) onto 3,5-di-tert-butylquinone (dtbq) showed that both complexes have moderate catalytic oxidase activity.Fil: Agotegaray, Mariela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Dennehy, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaFil: Boeris, Mónica Alejandra. Universidad Nacional de La Pampa. Facultad de Ciencias Veterinarias; ArgentinaFil: Grela, Maria Alejandra. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata; ArgentinaFil: Burrow, Robert A.. Universidade Federal de Santa Maria; BrasilFil: Quinzani, Oscar Valentín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; ArgentinaPergamon-Elsevier Science Ltd2012-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/199504Agotegaray, Mariela Alejandra; Dennehy, Mariana; Boeris, Mónica Alejandra; Grela, Maria Alejandra; Burrow, Robert A.; et al.; Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine; Pergamon-Elsevier Science Ltd; Polyhedron; 34; 1; 2-2012; 74-830277-5387CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0277538711007558info:eu-repo/semantics/altIdentifier/doi/10.1016/j.poly.2011.12.005info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:08:52Zoai:ri.conicet.gov.ar:11336/199504instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 10:08:52.405CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
title Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
spellingShingle Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
Agotegaray, Mariela Alejandra
ANTI-INFLAMMATORY
CATECHOLASE
COPPER
FENOPROFEN
SOD
title_short Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
title_full Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
title_fullStr Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
title_full_unstemmed Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
title_sort Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine
dc.creator.none.fl_str_mv Agotegaray, Mariela Alejandra
Dennehy, Mariana
Boeris, Mónica Alejandra
Grela, Maria Alejandra
Burrow, Robert A.
Quinzani, Oscar Valentín
author Agotegaray, Mariela Alejandra
author_facet Agotegaray, Mariela Alejandra
Dennehy, Mariana
Boeris, Mónica Alejandra
Grela, Maria Alejandra
Burrow, Robert A.
Quinzani, Oscar Valentín
author_role author
author2 Dennehy, Mariana
Boeris, Mónica Alejandra
Grela, Maria Alejandra
Burrow, Robert A.
Quinzani, Oscar Valentín
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv ANTI-INFLAMMATORY
CATECHOLASE
COPPER
FENOPROFEN
SOD
topic ANTI-INFLAMMATORY
CATECHOLASE
COPPER
FENOPROFEN
SOD
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The copper(II) ternary complexes of the non-steroidal anti-inflammatory drug Fenoprofen (Hfen) and the biologically relevant molecules imidazole (im) and caffeine (caf) as auxiliary ligands were investigated as novel anti-inflammatory agents. The new copper(II) complexes with formula [Cu(fen) 2(im) 2] (1) and Cu 2(fen) 4(caf) 2 (2) were synthesized from the dinuclear complex [Cu 2(fen) 4(dmf) 2] and characterized by IR, UV-Vis, EPR spectral and elemental analysis. The molecular structure of complex 1 was determined by X-ray crystallography. Both complexes 1 and 2 present enhanced and prolongued anti-inflammatory properties against the parent drug calcium Fenoprofenate, Ca(fen) 2·2H 2O, with a better performance for complex 1. Ternary complexes are potential models for several mono and poly-nuclear metal enzymes. The measured superoxide dismutase (SOD) mimetic activities of the complexes indicated a higher SOD mimic activity for complex 2 (IC 50 of 0.24 μM) than complex 1 (IC 50 of 0.70 μM), and also than the native enzyme evaluated by the same method (IC 50 of 0.480 μM). The catecholase activity of the complexes toward the aerobic oxidation of 3,5-di-tert-butylcatechol (dtbc) onto 3,5-di-tert-butylquinone (dtbq) showed that both complexes have moderate catalytic oxidase activity.
Fil: Agotegaray, Mariela Alejandra. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Dennehy, Mariana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
Fil: Boeris, Mónica Alejandra. Universidad Nacional de La Pampa. Facultad de Ciencias Veterinarias; Argentina
Fil: Grela, Maria Alejandra. Universidad Nacional de Mar del Plata. Facultad de Ciencias Exactas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Mar del Plata; Argentina
Fil: Burrow, Robert A.. Universidade Federal de Santa Maria; Brasil
Fil: Quinzani, Oscar Valentín. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Bahía Blanca. Instituto de Química del Sur. Universidad Nacional del Sur. Departamento de Química. Instituto de Química del Sur; Argentina
description The copper(II) ternary complexes of the non-steroidal anti-inflammatory drug Fenoprofen (Hfen) and the biologically relevant molecules imidazole (im) and caffeine (caf) as auxiliary ligands were investigated as novel anti-inflammatory agents. The new copper(II) complexes with formula [Cu(fen) 2(im) 2] (1) and Cu 2(fen) 4(caf) 2 (2) were synthesized from the dinuclear complex [Cu 2(fen) 4(dmf) 2] and characterized by IR, UV-Vis, EPR spectral and elemental analysis. The molecular structure of complex 1 was determined by X-ray crystallography. Both complexes 1 and 2 present enhanced and prolongued anti-inflammatory properties against the parent drug calcium Fenoprofenate, Ca(fen) 2·2H 2O, with a better performance for complex 1. Ternary complexes are potential models for several mono and poly-nuclear metal enzymes. The measured superoxide dismutase (SOD) mimetic activities of the complexes indicated a higher SOD mimic activity for complex 2 (IC 50 of 0.24 μM) than complex 1 (IC 50 of 0.70 μM), and also than the native enzyme evaluated by the same method (IC 50 of 0.480 μM). The catecholase activity of the complexes toward the aerobic oxidation of 3,5-di-tert-butylcatechol (dtbc) onto 3,5-di-tert-butylquinone (dtbq) showed that both complexes have moderate catalytic oxidase activity.
publishDate 2012
dc.date.none.fl_str_mv 2012-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/199504
Agotegaray, Mariela Alejandra; Dennehy, Mariana; Boeris, Mónica Alejandra; Grela, Maria Alejandra; Burrow, Robert A.; et al.; Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine; Pergamon-Elsevier Science Ltd; Polyhedron; 34; 1; 2-2012; 74-83
0277-5387
CONICET Digital
CONICET
url http://hdl.handle.net/11336/199504
identifier_str_mv Agotegaray, Mariela Alejandra; Dennehy, Mariana; Boeris, Mónica Alejandra; Grela, Maria Alejandra; Burrow, Robert A.; et al.; Therapeutic properties, SOD and catecholase mimetic activities of novel ternary copper(II) complexes of the anti-inflammatory drug Fenoprofen with imidazole and caffeine; Pergamon-Elsevier Science Ltd; Polyhedron; 34; 1; 2-2012; 74-83
0277-5387
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0277538711007558
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.poly.2011.12.005
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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